Journal ArticleDOI
Horsfiline, an oxindole alkaloid from Horsfieldia superba
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This article is published in Journal of Organic Chemistry.The article was published on 1991-11-01. It has received 351 citations till now. The article focuses on the topics: Horsfiline & Horsfieldia superba.read more
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Concise synthesis of (±)-horsfiline and (±)-coerulescine by tandem cyclisation of iodoaryl alkenyl azides
Dimitrios Lizos,John A. Murphy +1 more
TL;DR: A brief, efficient and economical synthesis of the spiropyrrolidinyloxindoles, horsfiline and coerulescine, has been achieved, starting from itaconic acid and, respectively, p-anisidine or o-iodoaniline.
Journal ArticleDOI
Microwave-assisted sequential amide bond formation and intramolecular amidation: a rapid entry to functionalized oxindoles.
TL;DR: A general method has been developed for the synthesis of N-substituted oxindoles through initial microwave-assisted amide bond formation between 2-halo-arylacetic acids and various alkylamines and anilines.
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Tandem Intramolecular Photocycloaddition−Retro-Mannich Fragmentation as a Route to Spiro[pyrrolidine-3,3′-oxindoles]. Total Synthesis of (±)-Coerulescine, (±)-Horsfiline, (±)-Elacomine, and (±)-6-Deoxyelacomine
TL;DR: Irradiation of a tryptamine linked through its side-chain nitrogen to an alkylidene malonate residue results in an intramolecular cycloaddition to the indole 2,3-double bond, which produces a spiro[indoline-3,3'-pyrrolenine] with relative configuration defined by the orientation of substituents in the transient cyclobutane.
Journal ArticleDOI
Pd-catalyzed assembly of spirooxindole natural products: a short synthesis of horsfiline.
TL;DR: The Pd-catalyzed intramolecular alpha-arylation of amides is applied to the synthesis of functionalized spirooxindoles and a new synthesis of horsfiline 1 is presented, giving the natural product in only 4 steps from commercially available amino acid 12.
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Regiodivergent Access to Five- and Six-Membered Benzo-Fused Lactams: Ru-Catalyzed Olefin Hydrocarbamoylation
TL;DR: It was found that while the selective cyclization was controlled primarily by the choice of catalytic systems employed, it was also greatly influenced by the structural nature of substrates.